Dundas Street: Introduction

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Welcome to Dundas Street. This photo blog is a bit different from my previous ones. Those followed hiking trails but this one follows a road, and I don’t recommend hiking along it. I’ll be taking the car. But I’ll often be found a little offroad, as that’s where much of the interest, historical and photographic, is located.

So, why Dundas Street? Because the original road of that name, a.k.a. Governors Road, is the most historic highway in southern Ontario. Dundas Street, running east to west, together with its north-south counterpart Yonge Street, formed the first colonial transportation network in what has become the most densely populated and economically dominant part of Canada. And I think you’ll find that the reasons for the construction of Dundas Street have increasing resonance today, more than two centuries later, especially as our neighbour to the south … no, I’ll let you draw your own conclusions.

Yonge Street was opened to link York (now Toronto), then serving as the temporary capital of Upper Canada (now Ontario), to the Holland River. It would replace the long-established Toronto Carrying Place, namely the system of waterways and portages between Lakes Simcoe and Ontario. Yonge Street was a relatively straightforward enterprise 53 km long, and it immediately opened up the area north of York for settlement. But Dundas Street was a much more ambitious concept. It was projected to eventually link Montreal, the main settlement in Lower Canada (now Québec), to Detroit, then a British-held fortress settlement,* a distance of more than 900 km. The project was never completed as conceived, though lengthy sections of Dundas Street west of York were opened at an early date. Still, Dundas Street is the key to understanding the early development of today’s southern Ontario.

*Detroit remained in British hands until 1796, well after the end of the American Revolution.

Why Dundas, and why Street? The answer to both questions can be found by examining the career of John Graves Simcoe (1752-1806), the first Lieutenant Governor of Upper Canada, in office from 1791 to 1796. Upper Canada had been created in 1791 by separating off the western portions of the Province of Québec, which was then renamed Lower Canada. In case you’re wondering, “Upper” and “Lower” refer to the two Provinces’ respective positions on the St. Lawrence, the great river being then the chief means of travelling between them. In those days, French-speaking, Catholic Lower Canada was by far the more established entity, and Simcoe’s office was junior to that of the Governor of Lower Canada, Guy Carleton, Lord Dorchester (in office 1785-95). By the creation of Upper Canada, the British Government hoped to encourage English-speaking Protestants to settle in a territory run on British lines.

In 1791 we are in the aftermath of the American Revolution. This had been concluded by the Treaty of Paris (1783), whereby the British formally ceded a large part of their North American empire to the American Republic. Aside from a small Native population, Simcoe’s Upper Canada was populated chiefly by Empire Loyalists, namely the relatively small percentage of Americans who preferred to continue to live under British rule and had moved, usually under compulsion, to the Niagara Peninsula.

Some of these refugees were Natives. The Six Nations of the Haudenosaunee (Iroquois) Confederacy, led by the Mohawk chief Joseph Brant, had allied with the British during the American Revolution. In retaliation, the victorious American rebels expelled the Six Nations from their traditional territory in New York State. The British, however, rewarded them for their loyalty to the Crown with an extensive territory along the Grand River. Please see my Grand River of Southern Ontario photo blog for much more on this issue.

“The Americans seem possessed with a species of mania for getting lands, which have no bounds. Their Congress, prudent, reasonable, and wise in other matters, in this seems as much infected as the people” (Cruikshank I, 98) – from a letter from Robert Hamilton in Niagara to J. G. Simcoe, dated 4 January 1792. Scottish-born Robert Hamilton was a wealthy businessman, judge, and politician whom Simcoe appointed to the Legislative Council of Upper Canada in 1792. Hamilton’s son George was the founder of the city of Hamilton.

Assuming office, Simcoe quickly realized that Upper Canada was in danger of being annexed, one way or another, sooner or later, by the United States. Only the Niagara River separated the thinly populated Loyalist settlements in the Niagara Peninsula from the USA. The first capital of Upper Canada, Newark (now Niagara-on-the-Lake), was within cannon’s range of the American border. Simcoe believed that the capital should be moved as far away from that border as practical. Military roads should connect the relocated capital to the Great Lakes so that troops could be moved quickly to and from ships to protect Upper Canada from American incursion.

Travel in early Upper Canada was easiest by ship on the Great Lakes and St. Lawrence River and by flat-bottomed “batteaux” and canoes along the major river systems. Inland there were Native trails, but no roads. Simcoe’s preference for the site of his new capital was at a major fork in the La Tranche (now the Thames) River, later the site of London, Ontario. He decided to cut his first military road from Coote’s Paradise, a marsh that forms the just-about-navigable western head of Lake Ontario, to the Thames. This road would give travellers access to Lake Erie via the Grand River – it would cross the Grand at what is now Paris – and to Lake St. Clair via the Thames River – which the road would meet at Oxford (now Woodstock).

So, this new road would allow troops to be moved inland to the Upper Great Lakes, avoiding the Niagara River and its extreme proximity to the USA. It would also offer a considerable shortcut to the Upper Lakes, as well as avoiding the lengthy portage around Niagara Falls. Simcoe’s fears about American invasion were justified. The Continental Army of the United States had unsuccessfully attempted in 1775-6 to capture the Province of Québec during the Revolutionary War, and Americans would repeatedly invade Upper Canada, also ultimately unsuccessfully, in the War of 1812.*

*For later manifestations of this kind, see The Annexation Bill of 1866, the Fenian Raids of 1866-71, War Plan Red, and this recent article.

The Queen’s Rangers, named for Queen Charlotte, wife of King George III, was a British regiment with its origin in the French and Indian War. Consisting chiefly of Loyalists under then Lieutenant Colonel Simcoe, they had distinguished themselves during the Revolutionary War and were known for their ability to operate in the harshest conditions. Simcoe revived the Rangers when he returned to North America in 1791. In 1793 he set them the task of cutting his first road from the head of Lake Ontario to the Thames River. We learn from the journal of Elizabeth Simcoe, wife of the Lieutenant Governor, that for a month from 23 September 1793, Captain Samuel Smith and 100 Queen’s Rangers opened a twenty-mile road from Coote’s Paradise towards the Grand River, having to kill numerous rattlesnakes en route (Innes 107). This, then, was the first colonial road in Upper Canada.

“The Governor’s Road, although blazed and cut, was barely passable by the time Simcoe left for England in 1796. One wagon’s width across at best, its path was set with boulders and stumps and it was sufficiently hazardous to both man and horse that Indian trails were frequently the better route – hence its grand name was a term of derision. Yet, the Governor’s Road (officially Dundas Street), with its eastern and western extensions, would become the spinal cord which supported the settlement of southern Ontario” (Byers 3).

Simcoe decided to name this first road after Henry Dundas (1742-1811), who in June 1791 had become British Home Secretary, an office which at that time was also responsible for colonial affairs, in the cabinet of William Pitt. Why? Several commentators have claimed that Dundas and Simcoe were friends, but I find no evidence of this friendship. Indeed, two biographies of Henry Dundas (Lovat-Fraser, Fry) do not even mention Simcoe. Rather, Simcoe would seem to have been an admirer of Dundas as a powerful and astute politician with whom it was best to stay on good terms. Dundas had long been the most powerful man in his native land – he was nicknamed Harry the Ninth, the Uncrowned King of Scotland. Simcoe believed that the Scots would make ideal immigrants to Upper Canada and citizens of his proposed capital, being Protestant, English-speaking, and above all used to harsh northerly conditions, as this memorandum to Dundas from Simcoe of 30 June 1791 makes plain:

“Emigration of hardy, industrious & virtuous Men may be reasonably expected from the northern parts of Great Britain. To settle these various descriptions of men so as to promote the cultivation of the Land, to give power & energy to civilization, Efficacy to just Government, & to combine a force whose appearance may prevent the very meditation of Hostility, It is indispensably necessary that a Capital should be established in some central situation and that as soon as possible, almost instantaneously, a great Body of Emigrants should be collected in its Vicinity so as to become the very transcript & Image of the British People & to transfuse their manners, principles, & attachments thro’ the whole Colony.” (Cruikshank I, 27)

Simply put, Simcoe believed a road called “Dundas” should attract Scottish settlement. In contrast, Henry Dundas himself believed that, aside from American Loyalists whose adhesion to the British Empire was not in doubt, immigration to Upper Canada from Scotland or elsewhere should not be encouraged, and wrote to Simcoe accordingly: “an ingrafted Population, (if I may so call it), to a great extent and outrunning, (as it must do), all those regulations, laws, usages, and customs, which grow up and go hand in hand with a progressive and regular Population, must I conceive in all cases be attended with a want of that regularity, and stability, which all, but particularly Colonial Governments, require” (Cruikshank I, 178). In other words, Dundas believed that a population of immigrants was likely to develop a desire for autonomy, as had happened in the USA, and would seek to throw off their colonial masters.

It has been claimed that as Henry Dundas never visited Canada, it’s absurd to memorialize someone with so little connection to the nation: “It’s worth wondering why Toronto has a street named after a Scottish politician who had nothing to do with its history” (Marshall 2021). However, the copious correspondence between Simcoe and Dundas reveals that the latter was knowledgeable about Upper Canada, followed Simcoe’s progress carefully, and generally gave him good advice. Lord Dorchester did not approve of Simcoe’s plan to relocate his capital inland to the Thames. Dorchester wanted the capital to be at York, a small fort constructed in 1793 on the shore of Lake Ontario about 65 km northeast of the head of Lake Ontario. Revolutionary France had declared war on Britain in February 1793, so it was not only the Americans that had to be feared, and Britain’s military strength was chiefly invested in its navy. Dundas advised Simcoe that York, boasting a fine harbour easily fortified and yet not too far – it’s directly across the lake – from Newark, would be the more suitable site for Upper Canada’s capital.

From Henry Dundas to J.G. Simcoe. Whitehall, 16th March 1794.
“I also agree with you that the Place upon the River Thames which you have marked as the scite [sic] for London, is well situated and judiciously chosen for the future Capital; but as the Defence of the Colony is the first Object, if that Defence should be Maritime, it follows that the Settlement of York is the most important for the present, not as the future Capital, but as the Chief Place of Strength and Security, for the Naval Force of the Province” (Cruikshank II, 185).

Dundas’s tactfully worded advice convinced Simcoe to give up on his original plan to relocate his capital to the Thames. You might say, then, that Henry Dundas had an instrumental part in the founding of present-day Toronto!

Only one section of Dundas Street has a high profile today. That’s the section that runs east-west through downtown Toronto, intersecting Yonge Street at what’s considered the very centre of the city, formerly Yonge-Dundas Square, recently renamed Sankofa Square. As we shall see, the downtown Toronto section of Dundas Street is a more recent creation, taking a different course from Simcoe’s original Dundas Street. But as part of a revisionist tendency that has led to the toppling of statues of once-admired historical personages, there has been a movement in Toronto to “cancel” Henry Dundas and rename places that bear his name. That’s because he has been accused of deliberately delaying the passage of an anti-slavery bill through the British Parliament.

From my understanding of the historical evidence, Henry Dundas was, like his admirer Simcoe, an abolitionist. In fact, Dundas had ensured that Scotland remained free of slavery and serfdom. As Lord Advocate of Scotland, Dundas had made a powerful speech in defence of Joseph Knight, a Black slave brought to Perthshire by John Wedderburn, who had made his fortune in the West Indies. Knight had married a Scotswoman and given his master notice that he intended to live freely with his wife and look for employment elsewhere. A court case, Knight vs Wedderburn, ensued, and in 1778 “on appeal to the Court of Session, where Dundas led for Knight, his emancipation was upheld … This established that slavery was illegal in Scotland” (Fry 59).*

*Joseph Knight is the subject of a novel (2003) by James Robertson and a play, Enough of Him (2023) by May Sumbwanyambe.

Henry Dundas did indeed advise that an anti-slavery bill proposed in 1792 should be revised so that its full implementation would be gradual. He did so because he felt that the bill would never pass through both Houses of Parliament until West Indies slaveholders were compensated for their losses. His prediction was unfortunately correct: while the House of Commons approved the amendments, the Lords, where vested interests were paramount, refused to support any reform of the status quo. The abolition of slavery in the British Empire was finally brought into full effect in 1834, but this delay was hardly the fault of Henry Dundas. Indeed, had his gradualist advice been followed, as it was by Simcoe (see below), abolition legislation might have been passed some years earlier.

Simcoe is justly praised for ensuring that Upper Canada was the first part of the British Empire to pass abolitionist legislation. But his 1793 legislation was designed to be implemented gradually, as Dundas had advised. Many of the wealthier American Loyalists who were early settlers in Upper Canada brought slaves with them and were very reluctant to give them up. Even the great Mohawk leader Joseph Brant employed Negro slaves at his houses at Mohawk Village and at Burlington! Autres temps, autres moeurs. The members of Simcoe’s legislature at Newark “belonged to the principal slave-owning class [and] were horrified at the thought of losing their most reliable source of labour” (Fryer 162). Like Henry Dundas, Simcoe understood that vested interests of the time were such that the abolitionist movement could only be successful if it progressed gradually. So slavery in Upper Canada was phased out over a twenty-five year period: “No more slaves could be brought into the province. Adult slaves in Upper Canada must remain in servitude, but children born to slaves would be free at age twenty-five, and their children would be free from birth” (162).

Why Dundas Street (rather than Road, or Trail?) The word Street for classically educated Britons of the time evoked the Roman occupation of Britannia. There were (and still are) many traces of “Watling Street” (444 km), “Dere Street” (364 km), “Ermine Street” (311 km), and other long-distance Roman military roads in England, 1,400 years after the Romans left. Street then was a name for highways that suggested successful and enduring colonization of formerly “savage” territory. Sir George Yonge (1731-1812), British Secretary at War from 1783-94, was something of an expert on Roman roads in Britain (Scadding 10). Simcoe and Yonge, fellow Devonians by birth, definitely were friends, and that’s how and why Yonge Street got its name.

What’s my skin in this game? I live in the town of Dundas, now technically a western suburb of the city of Hamilton. Dundas has a long history, longer indeed than Hamilton’s, and it is fascinating to trace how its location at the head of Lake Ontario made it, for a short time, the transportation hub of Upper Canada. The town was named for Dundas Street, not for Henry Dundas, and there is no statue in it to “Harry the Ninth” of Scotland. In fact, I’d wager that 99% of the town’s 25,000 population have no idea who Henry Dundas was. But they all do know that Dundas is an attractive and historic town, and many of them still resent its forced “amalgamation” with (i.e., absorption by) the much larger Hamilton in the year 2000.

Dundas, then, is a name with very positive connotations in the town, and very few Dundasians would wish to change it. However, in July 2021, Toronto City Council, having been persuaded that Henry Dundas was somehow involved in the transatlantic slave trade, voted to change the name of Dundas Street and associated infrastructure in that city. So far, Dundas and Dundas West subway stations have been renamed. Will the costs of renaming the street itself, of readdressing the 4,000 businesses along it, and of the inevitable controversy stirred up about any proposed new name, be worth incurring? Or what’s more to the point, should so historic a street name, that of a thoroughfare fundamental to the foundation of Toronto itself, be dropped, based on a false characterization of Henry Dundas?

If Torontonians until recently had thought about it at all, they’d probably have assumed Dundas Street was so called because it goes to the town of Dundas. And indeed, those sections of Dundas Street opened after 1814 (Woodhouse 2024, 41) did indeed lead to Dundas. That’s when the village previously called Coote’s Paradise took on its present name. So, if a short section of road between Dundas Street (Ontario Highway 5) in Waterdown and the town of Dundas were to be renamed or rebranded “Dundas Street,” that might help to dispel Toronto’s embarrassment. Dundas Street would then be so called because it goes to Dundas! And then Toronto could go ahead with renaming streets – such as Jarvis Street – that are named for people – like Samuel Jarvis (1792-1857) of the Indian Department – who really don’t deserve positive memorialization.

In this photoblog, I’ll begin, like the Queen’s Rangers, at Coote’s Paradise, and follow Dundas Street – which for some of its length is called Governors Road in memory of Simcoe – via Paris and Woodstock as far as the end of its later western extension at the fork of the Thames in London. Then, returning to Dundas, I’ll trace the course of the eastern extension of Dundas Street via Waterdown, Burlington, Oakville, and Mississauga, and follow it through downtown Toronto as far as its end at the intersection with Kingston Road in Toronto’s east end. I’ll also deal briefly with traces of Dundas Street east of Toronto, as well as with that part of Highway 8 in Cambridge which is also called Dundas Street.

I hope you enjoy the journey.

Part 1 coming soon